For Compounds Like CH₃OCH₂Cl, It Has Been Determined That

question 9

Short Answer

For compounds like CH₃OCH₂Cl, it has been determined that the gauche conformation shown here is lower in energy than the anti conformation, a phenomenon called the anomeric effect. One explanation for the anomeric effect is like the one provided for the lower energy of the staggered conformation of ethane relative to eclipsed ethane. This explanation invokes a stabilizing interaction between an empty orbital and a filled orbital in the gauche conformation of the molecule. The Newman projections shown here look down the central C-O bond:



One of the orbitals involved in this theory contains one of the oxygen lone pairs.What is the other
orbital?

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